


Bookstore Beauty

by ToManyFandomsToCount



Category: Supernatural
Genre: Abusive PAST relationship (Mentioned but not shown), Alistar is a dick, Bookstores, Bullying, Cas has a cat, Chubby Dean, Crowley is a dick, Dean Winchester Has Self-Esteem Issues, F/F, F/M, Insecure Dean, John has passed away, M/M, Mary Loves her boys, Mary is Busy, Meeting before the date, Nerd Dean, Protective Jo, Sam is a sweetie, Seriously someone just give Dean a hug, Slow Burn, Teen Dean, Wow these tags are all over the place, blind dates, caring Cas
Language: English
Status: In-Progress
Published: 2019-04-21
Updated: 2019-09-16
Packaged: 2020-01-23 08:04:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 11,565
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18545686
Author URL: https://archiveofourown.org/users/ToManyFandomsToCount/pseuds/ToManyFandomsToCount
Summary: No one would love a Fat Nerd like Dean, at least that's what his ex would tell him. But maybe the blue eyes angle who works at the bookstore can change that





	1. Chapter 1

**Author's Note:**

> Hello!! This is my very first FanFiction (so please be kind), I've always wanted to write something so finally, I'm trying, not sure how long the story will be but I promise there WILL be an ending if you have any notes or comments on how you would like to see the story progress let me know! :)

Chapter 1

“Come on Dean! Why can’t I set you up with someone? You’ve been single for over a year now, you deserve some lovin’” Charlie groaned as Dean grabbed his bag from his locker. He huffed in annoyance and looked at her.

“I don’t know, Charles, maybe it’s because the last guy you set me up with was…well…the last guy you set me up with”. A pit formed deep in Deans stomach at the memory. Charlie rolled her eyes, opting to overlook Dean calling her ‘Charles’.

“Firstly, I had no clue he was like that; and secondly; Let me make that up to you, please Dean you deserve to be happy”.

Dean laughs under his breath, happy? Him? No, he doesn’t deserve something as great as that. He closes his locker and the two of them walk down the busy hallways of Wayward High. Dean and Charlie are in their last year there, Charlie looking forward to graduating and pursuing a carrier in Science Fiction History, and Dean…well, Dean’s just happy to be getting out of there.

“I appreciate the enthusiasm Charlie, really I do, but I’m just not ready to see someone again”.

“Alright, what about one date? Please? Jo works with this guy and she says he’s really sweet, and that if she were into guys, she would-and I quote-‘hit that thang-“ Dean glances wide-eyed at Charlie who just nods back.

“You’re not gonna let this go are you?” He groans. Charlie quickly shakes her head.

“Fine! One date, that’s it. I gotta go grab Sammy, we still on for C.O.D on Saturday?” Charlie raises her thumb up as the two of them part ways. Dean makes his way down the stairs to Sam’s locker, all the while dreading what Charlie is once again, getting him into. As he walks down the halls he gets knocked by passing students; he’s invisible here, noticed only by the bullies and his small group of friends. While Dean never thought the stereotypical high school was a thing, this was it; all around Dean were cliques, the Jocks hung with the Jocks, Goths with Goths, and Dorks with Dorks; and deep within the Dork section of the cliques is Dean and his tiny group of friends, and even then there are times when Dean feels like the odd one out in that tiny group as well. He’s invisible to basically anyone and everyone. Well, except for.

“Heya Dean!” Sammy. Sam runs over to his big brother, who in turn shakes a hand through the tall boy's shaggy brown hair. The brothers walk down the halls, it's surprising really, the moment Dean is walking with Sam, people stop bumping into him, sure the hello’s are only directed to Sam, but it’s nice to not get shoulder checked every thirty seconds. They walk out of the school and to the only thing that has made sure Dean survives High school, the ’67 Chevy Impala (or ‘baby’ as it’s more commonly known) that Dean’s Dad had given him. Sam slides into the passenger seat, throwing his bag into the back.

“So Kiddo, how were your classes?” Dean asks as he pulls out of the parking lot.

“Good, good” Sam replies, staring intently out the window and not really paying attention to what Dean is saying; Dean can read his brother like a book and can tell that something important is on his mind

“What’s going through that big brain of yours?” He asks. Sam takes a deep breath, biting onto his lip.

“Could we stop at the bookstore?” This takes Dean by surprise, this was deemed important enough for all that thinking?

“Uh, yeah of course bud, you got a report coming up?” Sam shakes his head.

“We got a new kid in our class today, her name’s Eileen”

“Ah, you wanna impress her?”

“Not really, she’s deaf, I wanna grab a book on sign language so it’s easier to talk to her”. Dean looks over at his brother, he’s such a little gentleman, always caring for a girl and thinking of ways that would make things easier for her.

“Of course we can go man, how about after dinner?” Sam nods his head and continues to look out the window, this time with a little smile on his face.

…

Dean pulls into the driveway and unlocks the front door. Sam runs straight for his room and closes his door.

“Mom! We’re home!” Dean calls out as he takes off his jacket, but quickly realizes he’s not getting a response when he sees the note on the counter.

_So sorry darlings, the hospital asked if I could work a double, there’s lasagna in the oven, Dean set it to 425 and let it cook for half an hour, or until the cheese bubbles, I promise I’ll make it up to you boys, I love you. xo xo Mom_.

Dean chuckled to himself and set the oven for 425.

“We’re having Lasagna Sam!” He calls out. It’s not surprising that their Mom was working late, ever since John passed away, Mary has had to work almost 24 hours a day in order to keep the house that they live in, and insist that the boys focus on their studies during the school year and work over summers, all she asks of them is to keep the house tidy, which both of the boys have no problem in doing. Dean walks up the stairs and opens the door to his room. Dropping his bag onto his bed, Dean unzips it and takes out his books. The stove is shit anyway so it’ll be a while before the lasagna is cooked. As he stands back up and turns, Dean is faced with an unwanted sight in the mirror. Himself. How he loathes the reflection staring back at him, his nose wrinkles in disgust as he puts his hand onto his stomach and watches as it sinks into his shirt. He hates it, he hates the way his stomach swells over the waistband of his far too tight jeans, hates the love handles (he shutters at the thought of that word, and 18-year-old boy with love handles? that’s just wrong) that have formed just above his hips; he hates how big his thighs are and how the rub together and jiggle when he walks, how big-not in the right way-his butt is, hates how he rivals some girls' boob sizes in his school, his chubby arms, and his stupid, ugly fat face. Yep Dean is a loser alright, in every sense of the word. He sighs sadly as he pulls up his Game of Thrones T-Shirt, revealing his stomach; he turns to the side, hating how far his stomach sticks out that way, and takes a deep breath in, watching as his stomach slowly goes into itself. He puts his hand on it hating how soft the skin feels, oh how he wishes the fat to go away, what he wouldn’t give to just wake up one day and be 150 lbs instead of his…he doesn’t know how much he ways, but he knows it’s way more than 150.

“You’re bloody disgusting!” the bodiless voice shouts at him, a memory engraved in his mind,

“You’re a fucking Whale!” it shouts. Lost in the self-loathing trance that he often gets into when he sees his reflections, Dean nearly screams when he hears the gentle knock on his door.

“Dean, the stove went off”, Sam called through the closed door. Hastily Dean shoved his shirt back down, throwing on a flannel on top, he takes a look at himself and decides to wear a light jacket on top of that as well, he throws it own and sadly glances at the mirror

“that’ll have to do”, he grumbles to himself. He gives his stomach fat one last angry pinch as a lament effort to pull it away and grabs his keys and wallet, knowing Sam will want to go the moment they are done their food.

It doesn’t take long for the boys to get to the bookstore, Sam runs in the second the engine goes off. Dean is not far behind him, and the moment he walks in, he quickly sucks in his stomach, partly for his self-esteem, and partly because he is shocked by the mess of black hair, and the piercing blue eyes staring back at him.


	2. Chapter 2

**Summary for the Chapter:**

> Who is the mystery guy that Charlie is certain is perfect for our young scared Dean?

**Notes for the Chapter:**

> Hi everyone! I'm so glad so many people liked chapter one! this story may be a bit of a slow burn but I love establishing characters (This one's a bit shorter, chapter three will make up for it I promise)

Chapter 2

 

“Why are you always trying to play cupid?” Castiel groans with his phone pressed against his ear with his shoulder as he struggles to carry the box into his room. 

“Because it’s my calling in life!” She shouts. Castle rolls his eyes as he goes to grab another box. “I just moved into my own place, is now really a good time to be a matchmaker?” He says. Castiel has known Charlie for about a year and a half, he works with her girlfriend and the hyper redhead has taken an immediate liking to him. 

“Just go on one date with this guy, please?” My God, Castiel can hear the puppy dog eyes through his phone. 

“Fine, I’ll give this guy a chance, after that no more setting me up, my wallet still hurts after the whole ‘Bella” incident” 

“Yeah…that was a mistake, but this one’s different I promise”, 

“He better be, now I gotta go do a work out before my shift, talk to ya later Charlie”. Castiel hangs up his phone, laughing slightly at himself, he looks down and sees a black mess of fur doing a figure eight around his feet. 

“That girl’s gonna set me up with some sort of toad isn’t she?” He says as he scoops up the cat, who responds with a light Mew. Castiel sets Levi down on the bed and sits down beside him. “Welcome to your new home buddy. What’d ya think?” He says as he gestures to the small apartment around them. It’s a bit of a downgrade from his place with Bella, but it’s got running water, a stove, a toilet, and a shower; so it’ll have to do for now. Castiel gets up off of the bed, startling Levi slightly and begins his workout. This was probably the only good thing he got out of his relationship with Bella, she was a total health nut and would wake up at the crack of dawn every single morning, go for a run, and do some yoga, all before her classes, in the beginning this shocked and confused Castiel, until he started doing it with her, at first it was brutal, but the more he did it, the better he felt, and now that that crazy bitch is out of his life, why should he stop the one good habit that she had gotten him into. She wasn’t his first relationship, but for some time he thought she would be his last. Charlie introduced them a year ago and they hit it off fast, some say that they moved too quickly, and now that he thinks about it Castiel can see how it could seem that way. But to two teenagers fresh out of high school and going to close Universities, it made all the sense in the world to move in together. But their little heaven quickly became a piece of hell; not too long after they had moved in together, Castiel began to notice just how expensive of a lifestyle Bella was expecting. After he demanded that Castiel get rid of Levi and sell him to buy her a new hair drying, Castiel promptly put Levi into his cage, grabbed his keys, and walked out the door. He doesn’t blame Charlie for the relationship, he’s taken it as he takes most things in life, as a learning experience and nothing more. He does one more push-up and huffs back up to his feet. 

“What do you think? should I bother showering before work?” He says to Levi, who had rolled upside down on the bed. 

“Merm”. Says Levi in a low grumble, 

“Yeah you’re right, I should shower”. Castiel grabs his towel and some shampoo and heads to the bathroom. When he’s in there Castiel gets a glance at his reflection. He’s not a vain person, but ever since he’s been doing workouts daily and eating better he has noticed a change in his body, a change for the better. His muscles are more defined and noticeable, and on some days he swears that he can see his abs. He wasn’t fat before, but he was a little self-conscious, as are most people when it comes to their bodies, now he has found that he is far more confident with his appearance now. Castiel takes one final glance at himself before he turns the water on and hops into the shower.

 

…

 

The bookstore isn’t busy when Castiel gets there, then again it never usually is. Castiel puts his bag down in the back room, where he is greeted by Jo. 

“Hey Cas!” She says with a smile, Castiel smiles back 

“Hey Jo, how’s the place holdin’ up today?” 

“Oh you know, the usual old crowd, some inappropriate old women, creepy old men and Charlie stopped by during her lunch break”. The two of them walk out of the back together, Castiel takes one of the boxes that have been shipped and begins to unpack it. 

“Speaking of the redhead wonder, did she tell you that she’s trying to set me up with someone again?” 

“Yeeeaaah, ever since you told her you were bi, she’s been shouting the names of random people out at me” Castiel leaned back against the desk. 

“Do you know this guy?” Jo puts the last book away, nodding,

“Yeah I’ve actually met him quite a few times, he’s really nice, cute too, him and Charlie have been friends for years”. So, this guy is a long time friend of Charlie? Castiel has to make sure he takes that into account before he judges the guy; while she may not be the best at being a matchmaker, she is really good at picking her own friends. The front door dings so Castiel pretends to busy himself so the customer doesn’t think they’re slacking off. He expects it to be another older person, much like the most of their cliental, but when he raises his eyes to greet them into the store, he is met with the most handsome looking man he has ever seen in his entire life, looking back at him with blindly green eyes.


	3. Chapter 3

**Summary for the Chapter:**

> Jo cares so much about dean and is protective of him...but why??

**Notes for the Chapter:**

> Hi everyone! sorry for the delay, I had surgery and it's taken a long time to recover, but here's chapter 3 as promised

Chapter 3

Dean watches the man behind the counter as he waves hello. 

“Welcome to the New again bookstore, can I help you find anything today?” He asks in a deep voice. For a moment Dean forgets how to speak, thankfully though it’s at this time that Sam cuts in. 

“I’m looking for a book on sign language, do you guys have anything?” He asks. Castiel nods his head and walks around the counter. My god, he’s even more handsome close up. Dean tugs his jacket tightly around his midsection as the man walks closer to him and Sam. 

“Of course, they’re right over here”. Castiel guides them over to a corner of the store to a shelf labeled ‘languages’ is displayed. 

“It’s considered a language?” Sam asks Dean, which snaps him out of his shocked state. 

“Uh…oh yeah Sammy, it’s just like trying to learn French or Spanish”. 

“But it’s actually much harder than it seems. If this is your first time learning it I recommend this book”. Castiel reaches up and pulls a book labeled ‘ASL for beginners’ off of the top shelf, and no, Dean was not watching the mans muscles as he stretched his arm out to retrieve the book. Castiel hands the book to Sam, who opens it immediately and begins to read it. 

“Is there anything else you guys need at the moment?” Castiel asks, though Sam is already huddled in a corner, moving his hands along with the images in the book. 

“N-no, we’re good right now”, Dean says, hating his voice for catching in his throat. Castiel nods his head. 

“Alright, well if you guys need anything, my names Castiel”. He says as he walks back to the counter. Dean watches him from afar ‘Castiel’ Dean thinks ‘I’ve never heard a name like that before’. He looks over and sees Sam content with his book, and begins to wander around the store himself. 

“Dean!” He turns his head and sees the girl with long blonde hair walking towards him. 

“Hey Jo” He says with a smile, Jo wraps her arms around him, frowning immediately as she does so. 

“I thought I already told you Dean, nothing's wrong with you, you don’t have to do that”. She says, keeping a hand on his shoulder. Jo doesn’t say what she’s referring to, but Dean knows. He admitted to Jo a while ago about his struggles with his weight and self-confidence, after a long night of talking that resulted in her opening up about once being fat as well.

(8 months ago)

“Nope, no way Jo, I don’t believe you” Dean laughed as he took another sip from the cooler. Jo rolled her eyes at him. 

“Oh ye of little faith, why don’t you believe me” She said as she leaned back on the couch. Both of them were waiting for Charlie to finish her shift to surprise her with a Starwars Movie Marathon for her Birthday. Dean leaned forward, pressing his elbows into his knees. 

“Because…well, look at you, you’re beautiful and fit and work out basically all the time. I don’t believe you. Proof or it didn’t happen”. Jo rolled her eyes and pushed herself off of her couch, walking into another room. After a few minutes she came back, holding some photos.

“You have to promise me you won’t tell Charlie, I’m only showing you to prove a point, got it?” Her tone was very different from just a moment ago. Dean put his drink down and nodded as Jo handed him the photos. No way, these can’t be her; well that is that the face is definitely hers, but the body, it can’t be. 

“Jo…how old-“ 

“I was 17 in those pictures…17 and 230 pounds. I hated my life and my body; I tried everything I could to lose the weight, some healthy ways…some not so much. It got to the point where I would do almost anything to drop the weight; I met Charlie online while I was that fat. She didn’t know of course, and we hadn’t asked each other where we lived yet and I only gave a vague description of what I looked like. But I knew I had a thing for her and that one day I’d want to meet her. So I became dedicated to losing the weight”. She took a deep breath, wiping away the tears that broke through, Dean listened intently, not daring to make a sound. 

“I lost over 50 pounds before I felt okay enough to agree to meet her. I’ve never told her what I used to look like, and I don’t think I ever will”. They sit in silence for a while, Dean moved over and sat beside Jo, putting a hand on hers. 

“I’ve lost more weight since then, but it’s been gradual enough that she hasn’t noticed. Dean, I’m not telling you this for you to pity me, or to think that caring some extra weight is wrong. I’m telling you this because I was where you are now. I hated myself and how I looked. I can see it in your eyes whenever you glance down at yourself, or eat in front of other people. You’re a handsome guy Dean, there’s absolutely nothing wrong with you.” Dean looked from Jo, to the photo of the girl in the picture, She was smiling in the photo, but Dean recognized the look in her eyes, the pain and sadness of hating your own body. Just then they heard Charlie’s car pull up, Jo grabbed the photo from Dean’s hand and shoved it under the couch. 

“Don’t tell her”, she pleaded, Dean nodded and kept her secret from his best friend.

(Present day)

Jo walks with Dean around the store for a while, she asks how his final year is going, and he explains how grateful he is to be getting out of there soon. 

“Just remember, University can either be a shit show, or really fun”. He rolls his eyes at her. 

“How would you know? You didn’t go”. 

“No, but my friend over there goes, and he says there’s no right way to explain the experience,” Jo says as she sticks her thumb behind her, gesturing at Castiel as he has his nose stuck in an old looking book. A part of Dean hopped that Castiel was the guy that Charlie was setting him up with, but a part of him worries that if that’s the case, Castiel would take one look at him, laugh, then walk away. 

“So has Charlie told you about your blind date?” Jo asks, basically bursting at the seams trying not to blurt out what she knows. Dean laughs, 

“Oh yeah, she hasn’t shut up about it. If he’s anything like Alistar, I’m gonna take a hard pass”. He reaches up and grabs a book from the shelf. 

“I know the guy, and believe me, he’s nothing like that Dick”. Dean rolled his eyes. 

“He may have been a dick but at least he was honest”. Jo gapes at him. 

“Dean no that’s not-“ 

“Sorry Jo, I gotta get back to the house to get the laundry done. Sammy! You wanna get that book?” Sam shoots his head up and nods, running towards the counter. 

“Alright that’s going to be $8.50” Sam throws 10 dollars onto the counter and runs out the door before Castiel can give him his change. 

“Here, I’ll take that”, Dean says as he stretches out his hand, Castiel drops the change into Deans hand and watches as the man walks out of the store.


	4. Chapter 4

**Summary for the Chapter:**

> Sam is just too pure for this world

**Notes for the Chapter:**

> Hi everyone, sorry this took so long. This is kind of a short chapter but that's because I'm planning a BIG one for chapter five so stay tuned ;)

Chapter 4

 

“You did what!?” Dean yells as Charlie drops down into the seat beside his. 

“Come on Dean, it’s not like I sold your soul to the devil, I just gave the guy your phone number, he said he’ll text you once he’s done his classes”. Dean Drops his head onto his desk and groans.  Great. This’ll be Alistar all over again. 

The teacher walks in and soon English class starts. Dean can’t really pay much attention though, he’s to busy thinking, or dreading, the inevitable date with this guy that’ll surely take one look at Deans chubby form and laugh out loud. His classes drag on, though Dean pays little to no attention, only thinking about this date that is going to be happening. 

By the time his fourth period class ends, he has received no messages, ‘he must’ve known I was a fat loser’ Dean thinks to himself, however much Dean tries to convince himself he didn’t want to go on the date, a part of him was a little excited, it’s probably for the best though, better to be shot down before the guy even knows what he looks like, than using his looks for a reason to call off the date. With a bit of a heavy heart, Dean walks to the Impala, where Sam is waiting patiently for him. 

“So? How’d it go with Eileen? Was she impressed?” Dean laughs as they get into the car. Sam rolls his eyes, but a small smile appears on his face. 

“Yeah, she thought it was really sweet that I was learning it…but, um I kinda messed up one of the signs”. Dean glances one eye over to his brother. 

“Oh god, what’d you do?” 

“Well…to say thank you, you touch the tips of your fingers to your chin and move your hand out like this” Sam demonstrates the action. 

“But what I didn’t know was that it’s horribly similar to saying the F-word, which is you put your fingers _under_ your chin and flick them out…so when she leant me a pencil I meant to say thank you but…um…” 

“Oh, Sammy” Dean says, laughing between each word. Sam’s face burns red with embarrassment. 

“It’s not my fault! Why'd they have to make those two words so similar anyways! She didn’t take it personally though, the laughed and showed me the difference”. 

“Well that’s good, the last thing you wanna tell this girl is ‘fuck you’” He laughs. Sam pouts the rest of the way home, face still a bright shade of pink. Dean pulls into the driveway, not surprised to find it missing their Moms car. Sam hops out and runs into the house, 

“It’s tacos tonight Dean!” Sam cheer out the door. Dean laughs as he pulls his bag out of the car and walks into the house. The smell of seasoned ground beef, sour cream, and Salsa fill the room, causing Dean's stomach to growl angrily. 'Shut it fatty' he thinks to himself. Suddenly he feels his phone Vibrate. 

_Hi…Charlie gave me your number, she wants to set us up apparently._

Dean bites his lip nervously. ‘Shit, shit, shit’ he thinks as he walks right to his room and drops his bag on his bed.

“He actually messaged me” Dean Whispers.

_Uh, yeah apparently, she’s adamant about setting me up with someone._

Does that sound okay? is it to forward? Is it alright? After humming over the message he decides to hit send.

“Dean come on! It’s time for dinner”. “Coming” Dean calls, leaving his phone on the table.

…

 

“Mom makes the best Tacos!” Sam sighs as he reaches for his fourth, Dean smiles as his brother, still slowly working on his second. 

“Yeah, they’re pretty good” Sam looks at Dean concerned. 

“Why haven’t you had more?” Dean shakes his head. 

“Not that hungry” He lies, he’s starving, but the thought of shoving food down into his already too big stomach makes a pit inside of him. 

“I wish she was home more often” Sam mutters as he finishes piling things into his Taco; Dean gives him a sad nod. 

“I know buddy, I wish she was home more too. But she’s doing this so we can stay in this house, and go to school”, Sam nods though Dean can tell that his brother isn’t entirely content with that answer. 

“You go work on your homework bud, I’ll do the dishes,” Says Dean; it is supposed to be Sam’s night to do the dishes, but he sometimes has nights like this and Dean’s always a bit of a pushover to make sure his brother is as happy as possible. 

“And maybe while you’re at it you can practice the right way to say thank you” He Jokes as Sam runs up the stairs. The lanky teen sticks his tongue out at his brother before retreating into his room. 

By the time Dean cleans all the dishes and puts them away, he had nearly forgotten about the text message he had sent; until he glances at his phone. ‘Just get this over with Winchester’ he thinks to himself as he flips his phone over. To his surprise, and shock, there is a message back, multiple actually. 

_She’s been the same with me since I’ve known her._

_She says you’re a really sweet guy. I’m sorry if my first message was to direct._

This makes Dean laugh a little. 

“He’s almost as freaked out as I am” He mutters as he walks back into his room; ‘maybe this guy will be okay…Maybe he won’t care that I’m chubby’ he thinks hopefully as he lies on his bed. A guy can Dream, right? Unfortunately, dreams aren’t always what you want them to be. 


	5. Chapter 5

**Summary for the Chapter:**

> What happened between Dean and his ex? Maybe the effects are worse than he leads on

**Notes for the Chapter:**

> wanted to try a mostly text-based chapter, pretty happy with how it turned out

Chapter 5

 

_Dream - 1.5 years ago_

 

“God Dean, you’re really going to go to my Family’s dinner looking like that?”Alistar sneered. Dean looked at himself in the full-sized mirror 

“Does it not look good enough Dear?” He whimpered. Alistar rolled his eyes and walked behind Dean, angrily grabbing onto his stomach. 

“This Dean Winchester. This is what I’m talking about. My God, I might as well be dating a Hippo. The Clothes are Fine-“ 

“They’re a little tight-“ 

“That’s because you constantly shove food in that hole you call a mouth. I thought if I got you clothes that were smaller it would encourage you to lose that spare tire you have; I guess you’ll just have to go oozing out like play-doh”. Dean looked at his Boyfriend with Tears in his eyes. 

“Please…it’s to tight, it hurts” he whispered. 

“Fine! Change! But if we’re late because of you, you’re going to pay for it” Bath shouted. He stormed out of the room, leaving Dean alone to sob. Quickly he ripped off the clothes that were already close to ripping themselves,

“He loves me…He loves me…he loves me” He muttered to himself as he searched for different clothes. Finally, he found something that he thought looked decent enough. 

“Let’s go, Dean!” Alistar shouted. 

“Coming Dear!” Dean called out he took one more look at his reflection and quickly sucked in his stomach before leaving the bedroom. Suddenly everything around him has froze, the clock isn’t moving. The radio has stopped, everything is still. Tentatively Dean walks towards Alistar, 

“Darling? Is everything-“ Dean is startled when Alistar turns around; it is not his boyfriend, but another being entirely, a monster with red skin, black eyes, and fire for hair. 

“You’re Worthless Dean!” it’s voice booms. Dean collapses onto the ground, shaking. 

“I’m trying Darling! Really I am!” He cries. The monster laughs at him. 

“You’re pathetic! You’re nothing but a weak, fat Loser who will never have love!” It kneels down in front of Dean, putting his finger under Dean’s chin, forcing him to look up. 

“Do you really think you’d ever get rid of me? I’m deep in your mind where you can never get to. I’ll always be with you Dean; do you know why?” He leans in closer to Dean. 

“Because Deep down you know that you are nothing more than an Ugly, Fat, disgusting waste of life. You’ll always know because I’ll always be here to tell you”. 

Suddenly He grabs onto Dean’s neck, choking him; Dean thrashes, trying his hardest to get away, but it feels like there are 50-pound weights on his limbs, restricting him from moving, breathing becomes harder and harder until everything becomes black.

 

_Present-day_

 

Dean Lurches awake with a scream. His breathing is labored and he’s drenched in sweat. 

“Just a dream,” he tells himself. 

“Just a dream”. He looks around his room and checks the clock ‘2:43 am’, 

“as good of a time as any to get a drink” he whispers as he throws the covers off of his body and pads barefoot out of his room, carefully avoiding the mirror. He walks into the kitchen and opens the cupboard when soft voice nearly shoots his out of his own skin. 

“Honey are you alright?” Dean whips his head around to see Mary bathed in a soft glow from the kitchen light. 

“Yeah Mom, sorry if I woke you” He whispers. She gives him a soft smile and gives him a hug. 

“No worries dear; want to talk about it?” Dean shakes his head but finds himself sitting at the kitchen table. 

“Was it him again?” She asks, not daring to say his name. Dean bites his lip but nods embarrassingly. He’s 18 years old…18! he should not be going to his Mom because of Nightmares. 

“He will never get near you again Dean, you know that I will never let that happen. He was a foul, troubled boy who took his problems out on you”. She says as she takes his hand. 

“What if he was right though…what if I’m…” Dean looks down, not wanting to finish what he was going to say to his own Mom. Dean had Told Mary about what was going on after his last fight with Alistar; How he told Dean that he was Fat and Ugly, that the only reason he was with Dean was to do some ‘community service’. Mary had never seen red so quickly in her life; in a heartbeat, she raced to Alistar apartment. Gathered every single thing that Dean owned that was there, and cursed his ear off for treating her boy that way, and if she ever saw him anywhere near Dean again she couldn’t hesitate to call the police. 

“Dean Henry Winchester, now you listen to me,” she says, gripping tightly onto his hands. 

“You are not fat; you will be able to find someone who loves you for who you are and not someone who will force you into being someone that you are not. And as for Ugly; you are the most handsome young man I have ever seen…I blame myself everyday for not seeing it sooner…I should have not let you moved into that apartment with him…I should have noticed how he was tearing my sweet boy…” Mary wipes the tears off of her cheeks; Dean puts his hand on her shoulder. 

“It’s not your fault Mom,” He says, she smiles at him and gives him a kiss on the forehead. 

“You should get back to sleep sweetheart, you have school in the morning”. Dean smiles at his Mom, though he doesn’t get to see her much, he’s always grateful for the times that he spends with her. Dean walks back into his room and closes the door; knowing he won’t fall asleep again any time soon, he lays on his back, staring up at the black ceiling; the monster still screaming in his head. Minutes ticked by Slowly and Dean came to the realization that he wouldn’t be sleeping anytime soon; so he grabs his phone and tries to busy himself. Play an app? No, too tired for that; Text Charlie? Even she’d be asleep right now; Social Media? Hard pass, Dean’s seen enough beautiful people telling him ‘you too can look this good’ to last him a lifetime. For some reason, however, Dean finds himself opening messenger.

_Hey, sorry for not replying earlier, it’s been a bit of a busy day._

 

He looks at his message, not to forward but also not to over critical, after a moment he hits send and continues to try to go to sleep.

 

_Ding._

 

Dean wasn’t expecting any response any time soon, he turns his phone over, half expecting to see a spam email, when instead he gets a response to his message.

 

_No worries, I get it; why are you awake though? it’s pretty late…or should I say early?_

 

This dumb joke makes Dean chuckle 

 

_Nightmares, couldn’t sleep, why are you up?_

 

_Bit of an insomniac myself_

 

Dean thinks about his response for a moment, but as he’s thinking his phone buzzes again

 

_I was thinking, given that Charlie is hellbent on us going on a date, and seeing as we’re both awake, why don’t we get to know each other a little bit first?_

 

Deans breath catches in his throat, ‘he’s going to know what a fat loser I am’. Quickly he shakes his head ‘No, no, not if I explain things the right way’.

 

_Sure, for starters, my name is Dean, what’s yours?_

 

He waits patiently for the response, half hoping that the sender on the other end types in Castiel, but Dean knows that is a pointless dream, that beautiful guy dating a fat ugly loser? That kind of thing only happens in movies. But sure enough, Dean can help but feel a pang of disappointment when he gets his response.

 

_Dean…I like that name, Mine’s Chase_

 

_“_ It’s for the best” He mutters to himself. 

 

_What do you look like Dean? Maybe we can swap pictures?_

 

This immediately almost sends Dean into a Panic; 

“no, no, no, no, he can’t see me like this…maybe I should do it though…would be better to get shot down over text rather than in-person” he whispers to himself, for some reason though, Dean can’t bring himself to take the photo.

 

_Camera’s shit on my phone. Besides, I think Charlie would want the ‘shock’ factor for if and when we go on a date._

 

“Shock factor…that’s one way to put it” He hears the phantom voice in his head, causing a shiver up his spine just as it did when Balth would degrade him.

 

_She does love that veil of mystery; Sounds good, I’ll go first. I have black hair, blue eyes, tend not to shave so I have some stubble…let’s see, sort of slim, and I’m kinda tall I guess, about 6’3”_

 

_I have brown hair and green eyes, and Lots of freckles._

 

“Fat, ugly, a waste of space”. The bodiless voice whispers into Dean’s ear.

 

‘keep it vague’ he thinks to himself.

 

_That’s all?_

 

_Not really good at descriptions, Sorry_

 

He waits for Chase to respond, worrying with each passing moment that he gave to much away and he already knows that Dean’s not worth his time. Finally his phone buzzes.

 

_Are you Free Saturday Dean?_

 

His heart skips a beat. It’s happening, it’s actually happening.

 

_uh, yeah I don’t think I have anything going on_

 

Dean is all but shaking in his bed with shock and nerves, scared but excited at the same time.

 

_Perfect, it’s a Date._


	6. Chapter 6

**Summary for the Chapter:**

> Sam really is the best Brother. And someone PLEASE GIVE DEAN A HUG

**Notes for the Chapter:**

> Hello Lovlies!!!! I really don't know how to explain this chapter, I just started writing and stopped when I felt it was done, hope you like it

Chapter 6

 

Lunch rolls around and Dean and Charlie wait in line. 

 

“God Dean you look like death…maybe it was because you were having to much fun texting your new boyfriend?” She teases as she pokes his side in a playful way. Dean rolls his eyes 

 

“I only told you we made a date just so you’d get off my back” He groans as he grabs a Salad; Charlie looks at his plate, shocked and confused. 

 

“What? Man is that all you’re gonna have?” Charlie asks as she looks down at Deans sad little tray that consists of a water bottle and a Salad that was mostly just lettuce. 

 

“Don’t have much of an appetite today Charles” He says, which is half true, sure he wishes he could eat more, but after last night he doesn’t really feel very hungry, not to mention he needs to drop a couple of pound before Saturday. The two off them find the table currently being reserved by their other friend Kevin Tran and sit down. 

“Dean if you Don’t give me more information on how your talk went last night I will take your phone and look at it myself” Charlie urges as she slides a burger to Kevin who is to invested in his laptop to notice the food. 

“I will, just not yet” he replies, Charlie shrugs at his response, then takes a big bite out of some shitty cafeteria pizza. The three eat in silence for the most part, Charlie and Dean making hushed conversation so as to not disturb Kevin; as they talk Dean absentmindedly eats off of Charlie’s plate, she says nothing about this.

 

“Dean Winchester to the principles office please, Dean Winchester to the principles office.”

Charlie whips her head around and gives him a raised eyebrow which Dean responds with a confused shrug of his shoulders. Quickly though Dean stands and begins to make his way to the door, not before taking a couple more fries off of Charlie’s plate.

Dean walks up to the office and opens the door. 

 

“Good afternoon Dean, how are you doing today?” asks the receptionist behind the desk, he makes small talk with her for a bit until she tells him that he can go in. Dean knocks on the door

 

“Come in” The principle responds. Dean walks in 

 

“Hello Mr. Winchester” Says Principle Singer, Dean walks further into the office, confused.

 

“Hi sir, is there a problem?” He asks. Principle Singer lets out a sign before gesturing down to the seat in front of him. Dean looks down and is shocked to see Sam hunched low in the chair, attempting not to be seen by his big brother. 

 

“Sam!? What the hell happened!” He snaps, Sam bites his lip and looks up at his brother, revealing a black eye and a bruising cheek. Immediately Deans heart does a flip, he drops downin the chair beside Sam and begins to inspect him.

 

“It seems as though your brother got into a bit of a fight with a boy in your Grade, Crowley”. 

 

“It wasn’t my fault!” Sam shouts, mores to Dean than to the man behind the desk. 

 

 

“He was putting shit on your locker and laughing and I saw what he was putting and then…I didn’t mean to punch him it just sort of happened; the next thing I knew I was on the ground” Dean looks over at Principle Singer.

 

“What was he putting on my locker?” He asks dreadfully. Principle Singer hesitates for a moment, not wanting to show the older Winchester, reluctantly though, he pulls out a sheet of paper and hands it to Dean. It was a good thing he was sitting, because if he wasn’t he would have dropped onto the floor. On the sheet in his hands is a photo of himself in the mens locker room after gym class, just before he had put his shirt on and the caption read ‘I didn’t know they let Hippos into the school’. Tears welled up in Deans eyes before he could stop them; he felt sick to his stomach and wanted to run to the bathroom.

 

“Dean I wanted to assure you that this kind of behaviour is not tolerated at my school and it will never happen again-“ 

“That’s what you said last time when they put my face on a pig, or the time before that when they wrote ‘ugly’ on my locker in permanent marker”. Principle Singer bites his lip, not saying a word, Sam looks up at Dean in horror at what he just heard, and Dean looks down at the paper in defeat.

 

“Crowley has been suspended for the remainder of the week, if need be I can excuse you and your brother for the rest of the day”. This offers little comfort to Dean as he crumbles up the piece of paper.

 

“Come on Sam”. He says Dryly, Sam scrambles off of the chair and follows Dean to the Door.

 

“Dean wait”. Principle Singer calls out, Dean Stops with his hand on the doorknob. 

“This is the last time it will happen, you have my word”. Dean scoffs at this, not bothering to turn around. 

 

“That’s what you said last time too”. He says as he and Sam walk out the door, they walk past the receptionist and Dean gets a Glance at Crowley in the detention room, holding a red cloth on his nose, Crowley spots Dean as well and puffs out his cheeks, laughing at him through the closed door.

 

Dean Slams the car door as he drops in, Charlie and Kevin Come running out of the school, managing to grab Sam before he gets in. Dean watches as Sam reluctantly tells them what had happened, he supposes its better they found out from Sam before Crowley told the school, Charlie’s face goes red and he watches as Sam and Kevin grab onto both of her arms, holding her back from running in and stabbing Crowley herself, funny how a 5 foot 90 pound girl can quickly turn into the most terrifying thing in existence. Dean watches as she thrashes around for a bit, while finally settling down by picking Kevin in the arm, an act that’s not very uncommon. She gives Sam a big hug and Vulcan Salutes Dean through the window, to which he hesitantly reciprocates. Sam drops into the passengers seat and Dean starts the engine.

 

“Dean…”

 

“I’m not talking about it Sam” He says in a robotic tone.

 

“But Dean-“ 

 

“I’m not talking about it alright!” 

 

“NO!” Sam shouts, this startles Dean as he has hardly ever heard his brother scream like that, Dean pulls onto onto the side of the road and looks at his younger brother.

 

“How long has this been going on?” He begs, Dean sighs and pinches the bridge of his nose, not answering.

 

“Dean they called you fat and Ugly! Are you mad at me for getting angry that I heard them saying that about you?” 

 

“Yeah Sam I actually am!” He shouts 

  
“You got hurt Sammy…you got hurt defending something that isn’t even true” Sam looks at Dean for a moment, dumbfounded

 

“I…what?” Dean sighs and puts his head on the steering wheel ‘here it comes’ he thinks to himself, he takes a deep breath and looks at Sam.

 

“Bud…I’m Fat, your older brother is a fat ugly loser and I feel ashamed of that every day of my fucking life, I see the way people look when they see me grab you after your classes. Look at you, you’re tall, fit, selfless, smart, have a crush on a great girl and doing whatever you can to make that work out, and the worst thing in your life is me”. Dean takes out the crumbles photo and shows Sam. 

 

“This is what your older brother looks like Sammy…this is the truth”. Sam sits for a moment, not saying a word and not even looking at Dean. He shoves the photo back in his pocket and looks ahead.

 

“Can we go back to the bookstore Dean?” Sam asks after what feels like a lifetime of silence, Dean looks over and nods to his brother. 

 

“Yeah bud, whatever you want”. 

 

…

 

Dean pulls into the parking lot and turns off the engine, Sam steps out not saying a word, leaving Dean alone with his thoughts.

 

“This can’t be happening…how could I let Sam find out about all this” 

 

“Well look at you, it’s obvious he already knew”, Dean jolts with a start when he sees Alistar sitting in the seat beside him, Dean closes his eyes and clenches the steering wheel. 

 

“You’re not real” He mutters.

 

“Well I may not be here physically, but in your mind? Oh Momma that’s my home right there” He moves closer to Dean

“Now, let’s tally up the Day shall we? You lied to this guy Charlie wants to set you up with; stole food from her plate that she paid good money for, and you let your sweet little brother get the shit beat out of him because you look like a tub of lard in clothes”.

 

“I didn’t lie to him” Dean mutters. Alistar rolls his eyes.

 

“You told him nothing about yourself, imagine what he’ll think when he comes to pick you up on Saturday and sees jell-o coming towards him”

 

“…how much do I have to lose?” Dean asks meekly.

 

“50…at least” Dean’s heat shoots up

 

“By Saturday?! That’s in 4 days!” Alistar laughs out loud at this.

 

“So hop to it than hippo…and remember, I’m always with you, right here”. He touches Deans head then vanishes. With a Shakey sigh Dean opens the car door and walks into the bookstore. 

 

“hey Dean!” Jo calls, Dean looks up and tries to smile at her, but of course she doesn’t buy it. 

 

“Hey, you alright? She asks tentatively, Dean takes a deep breath before he lies through his teeth.

 

“I’m fine, where’s Sam?” Jo moves her head over to a corner

 

“He;s made a nest there, moved really quickly, I almost didn’t see him, why did something happen?” Just as if fate wanted to push Dean down any further Jo’s phone goes off.

 

“Hang on sorry, I know I shouldn’t have my phone out during work but I mean it’s just you and Sam here…hey babe” She says into the phone.

 

“Yeah actually Sam and Dean are here…no he hasn’t said anything to me…why what happened to Sam?” She whips her head around and looks intently at the corner where the lanky teen nestled himself into. Suddenly her face drops, Deadpan she turns and looks back at Dean. 

 

“I have to go, yeah more customers…love you too”. She hangs up the phone and looks over to where Sam is sitting, then looks at Dean. 

 

“Dean…I…” But Dean cuts her off by walking over to Sam. 

 

“You find something you like bud?” He asks, 

 

“A few, yeah” Sam says, not looking up from the book, Dean bites his lip, shame coursing through his veins. 

 

“He hates you” Alistar’s voices echoes in his mind. 

 

“Shut up” He mutters

 

“What?” Sam asks, Dean stammers 

 

“Oh uh nothing Bud, almost ready to go?” Sam nods

 

“Yeah…I think I’m gonna walk home though, if that’s alright with you I mean” Dean’s heart squeezes and feels like it’s going to burst, but on the outside he tries to be calm.

 

“Yeah bud, no problem, just uh…just be safe alright? I’ll see you at home” 

 

“Yeah” Sam says shortly. He goes up to Jo, pays for a few books, and leaves without looking back at Dean. 

 

“I’ll see you later Dean” Jo says hesitantly, Dean rubs his neck 

 

“He uh…he doesn’t want me to drive him home” The tears stream down before Dean can stop them and Jo ushers him into the back room, closing the door. 

 

“W-what about the store?” Jo shakes her head, 

 

“The monitor right there will tell me when someone comes in…besides this is more important” She sits Dean down and gives him a bottle of water. 

 

“He’s ashamed of me” He mutters Jo shakes her head. 

 

“No he isn’t Dean, for as long as I have known you I have only seen Sam look up to you with nothing but admiration and respect”. Dean chokes back a sob. 

 

“Come on Jo, you saw him just now he wouldn’t even look me in the eye…and I know Charlie told you what happened, how could I let Sam have such a fat big brother”. She takes his hand in her and gives it a tight squeeze, knowing Dean really doesn’t want an answer to his question. They stay like this for a moment, the only sound is Deans heavy breathing. 

 

“I need to lose weight” He says matter of factly, Jo looks at him. 

 

“How much?” She asks in a worried tone. 

 

“50 pounds at least…maybe 100, whatever it takes to get rid of this-“ He grabs onto his stomach “-before my Date on Saturday” Jo grabs onto his shoulders tightly, 

 

“Dean that’s impossible and you know it! You can’t lose 50 pounds in 4 days, especially not 100 pounds! either way that is way to much weight for you to think you have to lose!” 

 

“Well he’s not expecting this is he! He told me he’s slim, slim means he works out, we’d look like the number 10 together…he’s going to laugh in my face…maybe I should just cancel the date”. Jo pinches the bridge of her nose and sighs.

 

“Dean I know this guy, I’m friends with him, don’t you think I would have made sure that he wasn’t a shallow dick before Charlie started setting you guys up” He looks up at her, tears welled up in his eyes.

“What if I liked someone else?” This catches Jo off guard, the whole time she’s known Dean he has never once shown any interest in anyone as more than a friend.

 

“Really? Who? Do I know them?” Dean nods, 

 

“Yeah, he works here too…” Jo thinks for a moment, confused, her and Castiel are the only main employees, sure they have a couple people on-call but never regular hours. 

 

“What;s the guys name that she’s setting you up with. 

 

“Chase”. Jo simply nods.

 

“And who do you like”. Dean tangles his fingers together 

“…Castiel”. Jo holds her breath for a moment, trying her hardest not to react in anyway that make Dean think she’s mocking him.

 

“He’s really sweet, why don’t you tell him?” She asks. Dean quickly shakes his head. “Hell no, besides he probably has someone already, I don’t think Castiel-“ 

“What?” Dean’s heart seizes when he hears the deep voice, he turns around to see Castiel standing in the doorway, God, how much had he heard?

“Hey Cas, you're like a Dog, the second someone says your name you appear” Jo says as she rolls her eyes, Castiel walks in, taking in the scene of the young man crying in front of him.

“Everything okay in here?” He asks, taking a seat beside Dean. For a moment Dean forgets to breath; he sucks in his stomach as far as it’ll go and puts his arms around his waist for good measure. 

“N-nothing” He says, cursing his voice for betraying him. “I have to go” He says, standing abruptly and quickly walking out the door. 

“Bye Dean!” Jo calls behind him as she hears the front door close. Castiel looks confused at her. 

“Was he okay…Wait did you just say Dean!?” Castiel looks back at the door, watching as the Impala pulls onto the road, Jo nods, wearing a shit-eating grin on her face.

“Yes I did my oblivious friend” She says as she grabs a box of books and carries it out to the store, Castiel follows her. She watches as the wheels in Castiel’s head begin to turn, suddenly a small grin appears on his face.


	7. Chapter 7

**Summary for the Chapter:**

> It has finally arrived!! The big date is finally here, hopefully nothing can ruin our Poor Deans time

The past 4 days are hell, to put it completely honest; he’s nearly killed himself by working out too hard, causing the next day to be filled with unbearable pain; but Dean pulled through, he edged on, because there was no other choice for him, no other option, no way around the inevitable because he is too far in to back out of the date (not to mention he wouldn’t hear the end of it from Charlie), and because he needs to earn Sam’s admiration again. He has barely spoken a word to Dean since the incident at the school, can barley even look Dean in the eye anymore. 

“Did you want to go to the bookstore after dinner again Sam?” Dean asks as he pushes around his meatloaf, taking small bites here and there.

“No thanks”. Sam says, keeping his eye on his food. This is tearing Dean up inside, knowing that he’s let his little brother down is the most shameful thing that he’s ever gone through. 

“I have to go do homework”. Sam pushes out of the table and runs up to his room before Dean can even get out a word. 

“He can’t even be seen with me”. Dean whispers to himself; he decides to put his food in the fridge, an action he’s been doing a lot lately and has caused his Mom to ask if he’s feeling alright. He walks into the bathroom and slips off his shirt, keeping his eyes closed as he steps onto the scale “Please be lower, please be lower, please be lower” He whispers as he keeps his eyes shut, knowing eventually he’ll have to open them. Reluctantly Dean opens his eyes and his heart clenches. 

224.

That’s it? 6 pounds? That can’t be all that he’s lost. Dean bangs his fits against the wall and steps off of the scale, looking in the mirror. ‘How did I let myself get like this’, he grabs onto his tummy and squeezes it meanly, ‘how could Chase think this’ll be attractive, how could I even think that Castiel would consider being with me…’ 

“looks like I’m ugly, fat, and stupid now too,” He says aloud, suddenly he hears a knock on the door. 

“Hang on Sammy!” Dean Calls as he struggles to get his shirt on, but Sam: being a younger brother and not bothering to listen, coms in anyways. “Damnit, Sam! Personal space!” Dean yells as he struggles with his shirt, Sam though seems unfazed. 

“Dean listen…I’m sorry I’ve been ignoring you the past couple of days, it’s just that-“ 

“You don’t want a fatty as a brother, I get that-” 

“Dean stop! You’re not some horrid being that has to be hated and ridiculed, you’re an 18-year-old kid who hasn’t exactly had an easy time what with Dad passing away and Mom working all the time”. 

“That stuffs hard for you too” 

“I didn’t really know Dad…and Mom working a lot is easier for me because of you doing so much to make my life easier…the hardest year for me was when you moved in with that Dick Alistar, and don’t say nothing happened cause I asked Mom about it and she told me what a messed up guy he was”. Dean looks at Sam for a moment, lowering down so he’s sitting on the edge of the bathtub. “I also know that you have a date tonight…and just…just don’t let him tell you you’re not good enough Dean”. Tears well up in Sam’s eyes, Dean gets to his feet and gives him a big hug. 

“You’re the greatest big brother in the world Dean, no matter what you weigh or how you think you look” Dean sighs as he pats Sam on the back, fighting back tears of his own. 

“Alright Sammy, this is enough chick flick shit for me; go do your homework”. Sam takes a step back an embarrassed grin on his face. “Actually…I’m kinda going out myself on a date, type…thing” Dean claps his hand on Sam’s should and smiles. 

“Atta boy! so the thing with Eileen worked out?” Sam’s smile grows bigger as he nods his head. 

“Yeah, we’re seeing a movie tonight…Close captioned of course”. Dean laughs “Yeah so I actually gotta go now, her mom is picking me up, I’ll see you later right?” 

Dean nods, “Yeah kiddo obviously, I’ll be wanting to know about how it goes”. Dean smiles to himself for the first time in days as he hears Sam run around the house, grab his jacket, then close the front door. 

“44 pounds to go darling; how are you going to manage to pull that off in the next 3 hours?” Dean sighs defeatedly and turns back to the mirror, where Azriel stands. 

“You lied. Sammy doesn’t hate me.” 

“No, no, you’re right love he doesn’t hate you…he just pities you, and really is that much better?” Dean looks back at the door. 

“He’s going to laugh at your face the moment he sees you, and you think you actually deserve to have a crush on that Castiel guy? HA!” Alister throws his head back and laughs out loud. So loud that he’s surprised no one else can hear him. Dean grabs onto his stomach, staring at the mirror, his heart, which was higher moments ago, now feels like a rock-filled with sinking dread.

It takes Dean longer than he’d like to admit to finding something to wear, all his button-ups pulled at the middle, making it seem like he was going to burst at the seems; he shutters when he thinks about that, remembering his nightmare. He gives up on the button-ups and tries some of his T-Shirts, he finds an old AC/DC shirt that actually belonged to his Dad and puts it on. It’s still bigger on him, but he can’t ignore how the material still stretches slightly in his midsection, Dean finds a pair of his nice jeans that fit him (A little tightly but they’ll have to do). He looks in the mirror and sighs sadly, he wishes he could look nicer for this date, but this’ll have to do, he throws a flannel on over the T-shirt to hide his rolls and puts on a jean jacket as well for good measure. As he stares partly defeated at the mirror his phone goes off, a text from Charlie.

_Go get some!_

 

They had agreed to meet up at a Starbucks and start the date from there, so Dean orders himself a coffee and sits nervously at the table as he waits for Chase to arrive. 

“It’s getting kinda late isn’t it tubby?” Alister voice whispers in his ear. 

“Shut up” Dean hisses under his breath. 

“He probably came in, saw you, said ‘fuck that’ and got his ass outta here,” Alistar says with a laugh, just then a familiar voice pulls him from his trance. 

“Hello Dean”, he looks up and sees Castiel waving at him, he shyly waves back. 

“Hi Castiel, what are you doing?” 

“Got a date, we’re meeting here”, he says as he slides into the empty seat in front of Dean. 

“Lucky girl,” Dean says with a smile

“Guy actually, and I don’t know about lucky; and what are you doing here?” Castiel asks, sounding a little bit Coui, 

“I’m actually waiting for a date too…he works with you and Jo”

“Oh yeah? Who’s the guy?” He asks with a smirk,

“Chase” Castiel tries to stifle a laugh but it doesn’t get past Dean, he winces slightly, thinking the laugh was directed at him. 

“What did chase tell you about himself?” 

“He said he has black hair, blue eyes, doesn’t really shave…slim… kinda tall…Oh my god” Dean can’t keep his mouth from falling open when the pieces connect in his mind. Castiel lets out a happy laugh. 

“I was wondering how long it would take you,” He says. 

“But you…you said that…the name wasn’t…” Dean stammers, not able to collect his thoughts. 

“It was a typo, iPhones don’t think Castiel is a real word apparently, didn’t notice until Jo pointed it out” Dean looks down at his hands, clenching his coffee so tightly it could break. 

“How long did you know it was me you had a date with?” He asks. 

“Not long, after you left the bookshop a few days ago and Jo said your name, that’s when I pieced it together” 

“And you till wanted to come?” Dean said with a slight chuckle, more to himself than to Castiel. 

“Of course I wanted to come, why wouldn’t I?” He asks, sounding a little serious, Dean waves the seriousness with his hand.

“No reason, just probably wasn’t what you were expecting was it”. A crease forms between Castiel’s brows. 

“No, I didn’t really have much of an image of you, you didn’t really give me much to go off of, and when I found out, I talked to Charlie and she spammed me with pictures of you and her, not to mention she gave the whole ‘if you hurt him I’m gonna kill you’ speech” 

“Yeah…that little red-head is a ball of fire” Dean laughs, Castiel laughs as well and moves his hand forward to Deans, resting it lightly on top. 

“Wanna go for a walk?” he asks, Dean takes another sip of his coffee and nods happily. The two of them walk downtown, talking about the bookstore, Jo, and of course, Charlie 

“Yeah she basically threw your number at me” Castiel laughs, Dean enjoys seeing Castiel smile, likes the way it shows of his white teeth and how soft and gentle it makes him look; for once Dean is enjoying himself and has mostly forgotten about being self-conscious, that is, however, until his stomach decides to betray him and growl loudly. ‘Shit’ Dean thought to himself, he wraps his arm around his stomach, hoping to God that Castiel didn’t hear, if he did though, he isn’t acting like it. 

“Hey, let’s go grab a bite, I know I good place right over here” He says; then Castiel does something that makes Dean’s breath catch, He grabs onto his hand and holds it firmly, He guides the shocked and a little bit giddy Dean to a small diner just around the corner and they go inside. 

“This place is really cute,” Dean says as he holds up the menu, trying to avoid his hands shaking from nerves. 

“Yeah, I used to come here all the time” 

“Why’d you stop?” Dean asks, opting to just put the menu down and focus on the handsome man in front of him. Castiel rubs the back of his neck, 

“Well…my Girlfriend-ex Girlfriend just so we’re clear, was a little bit of a health nut and swore off this place because they sell greasy food and milkshakes”, 

"He brought you here cause you’re a fat pig and he wants to laugh at the fatty eating" Alistar hisses into Dean’s ear, he tries his best to ignore it. 

“How’d you guys meet?” Dean asks, hoping it wasn’t a to demanding question, apparently it wasn’t 

“It was about a year and a half ago, Charlie was actually the one who sees us up, at first it was great…and then…well, let’s just say that shit hit the fan in every way possible up to shit actually hitting a fan”, Dean laughs a this, causing him to choke a bit on his water. 

“Yeah…she’s not exactly the worlds greatest match maker” 

"yeah, for instance, you and this handsome fit greek god," Says Alistar Castiel closes his menu and leans closer to Dean. 

“What about you? did Charlie ever set you up with someone…other than me” he adds the last part with a laugh, Dean, however, doesn’t feel like laughing, his chest tightens and his breathing becomes labored, immediately Castiel notices this and grabs onto Dean’s hand 

“Dean…Dean hey you’re okay, just take a deep breath, drink some water, you’re okay” He shakily grabs his glass and takes a long drink. After a moment of letting Dean catch his breath and calm down, he finally speaks. 

“S…sorry about that…It was just-“ 

“No need to explain, if it’s something you don’t want to talk about than we won’t talk about it”. Dean sighs with relief. The rest of the night goes fairly smoothly, though Dean gets a questionable look from Castiel when he orders a small Garden Salad with no dressing, he doesn’t question the other man's actions and orders a cheeseburger and fries for himself. After some light conversation, and Dean sadly eating his salad (and maybe taking a couple fries from Castiel’s plate) They split the bill, and walk out of the Diner. 

“Are you sure that was enough food for you Dean? That was a really small Salad, and you seemed pretty hungry when went in”, Castiel asks, concern written on his face. 

“Oh yeah I’m good, it was actually more than I realized, almost couldn’t finish it all” He lied, he was still starving. Hopefully, his Mom saved him an extra plate so he could eat it when he got home. The two walk for a little longer, then stop and take a seat on a park bench, Castiel sitting a little to close to Dean for his liking. Neither say anything for a while until Castiel breaks the silence. 

“Ya know I was actually pretty nervous about this date” He admits, Dean looks at him, 

“Those nerves probably went away when you figured out who I was right?” He says with a light laugh, Castiel however, doesn’t see what was funny, 

“No, if anything it made me more nervous, you’re just-and I’m sorry if I’m being to forward Dean-but you’re just so Handsome, I was quite intimidated” So, the first Date and Castiel has already lied to him…granted probably the first and only date but still good to know. 

“You were intimidated by me? look at you! I didn’t think a guy like you could be intimidated by anyone” Dean says, gesturing at Castiel’s face to further his point, this makes Castiel blush slightly in embarrassment, something that makes Dean find him even cuter. 

“Could I-um…I’d really like to know if I could…but if you don’t want to that’s totally okay, but I was wondering if I could….kiss you, Dean?” Dean smiles and gives him a small nod. Castiel grabs onto Dean's hand and slowly leans forward, placing his lips against Dean’s. As soon as their lips touch a warmth erupted within Deans chest, he never knew that a kiss could be so gentle and so passionate at the same time, his lips are so soft and warm against Dean’s, he lets himself melt into the kiss, moving his hand onto Castiel’s knee, who moans in response and rests his hand onto Deans Side. Unfortunately, that is what forces Dean to stop. His eyes fly open and he quickly bats Castiel’s hand away, pushing himself to the opposite side of the bench, Castiel stares at Dean, shocked and confused. 

“Dean? Dean are you okay? I’m sorry Dean I didn’t mean to go to-“ 

“I’m sorry Castiel…I have to go get my Brother…thanks for the date. Bye”. Dean shoots up off of the bench and quickly walks to where the Impala is parked, tears streaking down his face as he leaves a shocked and bewildered Castiel at the park bench.


End file.
